Catalytic Enantioselective Protonation of Enol Trifluoroacetates by Means of Hydrogenocarbonates and Cinchona Alkaloids

被引：30

作者：

Claraz, Aurelie

Leroy, Jerome

Oudeyer, Sylvain ^{[1
]}

Levacher, Vincent

机构：

[1] Univ Rouen, CNRS, UMR 6014, F-76130 Mont St Aignan, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 15期

关键词：

KETENE DISILYL ACETALS; ASYMMETRIC PROTONATION; MICHAEL ADDITION; ACID; ETHERS; HYDROLYSIS; ESTERS; DERIVATIVES; AMINES; SCOPE;

D O I：

10.1021/jo201146b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein is disclosed an efficient catalytic enantioselective protonation of enol acetates by means of a readily implementable transition-metal-free chemical process. By making use of simple hygrogenocarbonates as the proton source and hydroquinine anthraquinone-1,4-diyl diether as the chiral proton shuttle, a series of cyclic enol trifluoroacetates are protonated under mild conditions to yield the corresponding ketones in up to 93% ee.

引用

收藏

页码：6457 / 6463

页数：7

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